1-Propanol → 3-Pyrimidinecarboxylic acid methyl ester

HRID 383125Notes

Reaction equation

HRID 383125 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH2:8]([OH:11])CC.C(N(CCCC)CCCC)CCC.CN([CH:28]=[O:29])C>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:28][O:29][C:8]([N:4]1[CH:3]=[CH:2][CH:7]=[N:6][CH2:5]1)=[O:11]

Participants

7

Reactant 4

HCID 10311-PropanolHCID 6228DimethylformamideHCID 7622TributylamineHCID 783445-Bromopyrimidine

Product 1

HCID 702124973-Pyrimidinecarboxylic acid methyl esterYield 52%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromopyrimidine (1.59 g, 10 mmol), 1-propanol (1.5 mL, 20 mmol), bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.50 mmol) and tributylamine (3.72 g, 20 mmol) in DMF was stirred at 90° C. under a carbon monoxide balloon for 10 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with potassium dihydrogenphosphate (1.0 M, 20 mL, twice), water, and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was then purified by column chromatography (50:50:10 hexane-dichloromethane-ether) to give 3-pyrimidinecarboxylic acid methyl ester (715 mg, 52%).

Workup

  1. washwashed with potassium dihydrogenphosphate (1.0 M, 20 mL
  2. dry with materialtwice), water, and brine, dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by column chromatography (50:50:10 hexane-dichloromethane-ether)

Sources & evidence

ORD record
ord-3d5b357006ee49468287373486b847cf
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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